Lace and Discovery at Fifty

I never thought my fiftieth birthday would involve a room full of cross-dressers, but here I am, standing in the doorway of Tyson's rented mansion, wearing a black lace bra underneath my dress shirt, feeling the elastic straps dig into my shoulders like a secret I've been keeping for months.

You're the one who got me into this, Tisa. You and that goddamn ziplock bag.

"Relax," you whisper in my ear, your hand squeezing my arm. "You look like you're about to bolt."

"I'm fine," I say, but my voice comes out thin and reedy, nothing like the voice of a man who once ran a sales team of thirty people.

You're wearing a red slip dress that barely covers the tops of your stockings, and I can see the outline of the black panties underneath — the same style you gave me that afternoon, the ones I pressed to my face before you even arrived. The memory makes my cock twitch inside my slacks, and I shift my weight, trying to look casual.

Tyson appears from the crowd, grinning wide, wearing a corset and a garter belt over his broad, hairy chest. It shouldn't work, but somehow it does. He looks like a Renaissance painting that got drunk and raided a Victoria's Secret.

"Mark! Fifty years old and finally ready to party!" He pulls me into a bear hug, and I feel the boning of his corset press against my chest. "Tisa, you magnificent creature, thank you for bringing him."

"He almost didn't come," you say, smirking.

"I almost didn't," I confirm.

The house smells like perfume and weed and something frying in the kitchen. Music pulses from speakers I can't see — something slow and bass-heavy. Everywhere I look, there are people in lingerie, in bras and panties, in full makeup and wigs, in nothing but garter belts and smiles. Some of them are beautiful. Some of them look like middle-aged accounters in ill-fitting teddies. All of them seem completely at ease.

I feel like I've wandered into someone else's fantasy and accidentally made it mine.

You lead me through the crowd, introducing me to people whose names I immediately forget. A tall cross-dresser named Delilah kisses me on both cheeks. A couple in matching pink chemises clink glasses with us. Someone presses a drink into my hand — whiskey, neat — and I take a long swallow, feeling the burn settle my nerves.

"I need to tell you something," I say, leaning close to your ear.

"You're wearing the bra I gave you?"

I pull back, surprised. "How did you know?"

You laugh, and it's that low, dirty laugh I've come to recognize as the precursor to trouble. "Because I know you, Mark. I know what you do when no one's watching. I know you tried on the panties, too. I know you stood in front of your bathroom mirror and felt the lace against your skin and got hard."

My face is hot. I take another drink.

"That's the whole point of tonight," you say, touching my chest, fingers tracing the edge of the bra strap through my shirt. "No more mirrors. No more hiding."

A woman — or rather, a cross-dresser who calls herself Matissa — approaches us. She's wearing a sheer black babydoll and nothing else, and I can see the outline of her cock through the fabric, soft and resting against her thigh. She's tall and elegant, with long legs and a messy blonde wig.

"You must be the birthday boy," she says, her voice a husky contralto.

"He is," you answer for me. "Fifty today."

"Fifty." She looks me up and down, and I feel it like a physical sensation. "That's a good age. Old enough to know what you want. Young enough to still get it up."

I laugh, despite myself. "I appreciate that."

"Tyson told me about you," Matissa continues, stepping closer. "Said you've been exploring. Said you've been wearing lingerie under your clothes at work."

I glance at you. You shrug, not even pretending to be innocent.

"I might have mentioned it," you say.

"To Tyson?"

"To Tyson. To Kayla. To literally anyone who would listen. I'm proud of you, Mark."

The whiskey is warming my blood, and the music is slowing down, and Matissa is standing close enough that I can smell her perfume — something floral and sharp, layered over the musk of bare skin. My cock is half-hard, and the lace of the bra is scratching my nipples, and I feel like I'm standing on the edge of something tall.

"There's a room upstairs," Matissa says. "Private. Tyson set it up for your birthday. If you want."

I look at you. Your eyes are bright, and your tongue is touching your lower lip, and I know that look. That's the look you had when you handed me the ziplock bag. That's the look you had when you watched me hold your worn panties to my face.

"I want," I say.

The upstairs bedroom is large and warm, lit by string lights and candles. The bed is king-sized, covered in dark sheets. There's a chair in the corner, and you sit in it, crossing your legs, your red dress riding up your thighs. You look like a queen settling in to watch a show.

Matissa follows me in, and behind her, three others — cross-dressers I barely noticed at the party. One is petite, wearing a purple corset and fishnet stockings. One is broad-shouldered, in a white lace teddy that strains across his chest. The third is slim and dark-skinned, wearing nothing but a pink garter belt and stockings, his cock hanging thick and heavy between his legs.

"Happy birthday," the slim one says, and grins.

My mouth goes dry. My heart is hammering. I turn to look at you, and you're leaning back in the chair, one hand resting on your inner thigh, and you give me a small nod.

Matissa steps behind me and starts unbuttoning my shirt. Her fingers are quick and sure, and I feel the air hit my chest as the fabric falls open. The black lace bra is fully exposed now, hugging my chest, the cups slightly too small, the straps pulling against my shoulders.

"Look at that," the broad one says, voice appreciative. "Beautiful."

Matissa slides the shirt off my shoulders and unfastens my pants. I step out of them, and now I'm standing in front of four cross-dressers and you, wearing nothing but a black lace bra and the panties you gave me — the ones that still carry a trace of your scent, woven into the fabric.

"Oh, fuck," I say, and it comes out almost reverent.

"Sit on the bed," you say from the chair, and I do.

The mattress dips as Matissa sits beside me. She reaches out and traces the edge of the bra cup, her fingertip brushing my nipple through the lace. I shudder, and my cock, already straining against the panties, jerks.

"You've never been with a cross-dresser before?" she asks.

"No."

"Never sucked a cock?"

I swallow. "No."

"Would you like to?"

I look at you again. You're smiling, and your hand has moved higher on your thigh, and I can see the dark triangle of your panties under the red dress. You're enjoying this. You're loving every second of my unraveling.

"Yes," I say.

Matissa stands and steps in front of me. Her cock is right there, at eye level, half-hard and thickening as I watch. She pulls the babydoll up and over her head, and now she's naked except for her earrings, her body lean and masculine in contradiction to the feminine way she holds herself.

"Go slow," she says. "Use your tongue. Let your lips do the work."

I lean forward. My hands are shaking, but when I wrap my fingers around the base of her cock, it feels natural — warm and alive, the skin soft over the hardness underneath. I bring my mouth to the tip and taste salt and skin and the faint sweetness of lotion.

I take her in.

The sensation is overwhelming — the weight on my tongue, the stretch of my lips, the way she twitches when I suck gently. I'm clumsy at first, using too much teeth, not enough wet, but Matissa guides me with her hand on the back of my head, and I learn.

"Fuck, that's good," she breathes. "You're a natural."

I hear you moan from the chair, and I look sideways without releasing her cock. You've pulled your dress up, and your hand is inside your panties, and you're touching yourself while you watch me suck. The sight sends a jolt through my body that lands directly in my groin.

The other three cross-dressers move closer, standing around the bed, their cocks hardening as they watch. The slim one is stroking himself slowly, his dark hand wrapped around a cock that's bigger than I expected. The broad one is playing with his nipples through the white lace. The petite one is kneeling on the bed behind me, running a hand down my back.

"That's it," Matissa says, her hips moving now, pushing deeper into my mouth. "Take more. You can take it."

I try, and I gag, and she pulls back, and I try again, and this time I take her almost to the root. My eyes are watering, and my cock is throbbing against the lace of your panties, and I've never been so hard in my life.

"Enough," Matissa says, pulling out. "I want to fuck you."

My stomach clenches. I look at you.

You stand up from the chair, your dress wrinkled, your lips parted. You walk to the bed and sit beside me, taking my face in your hands.

"You want this," you say. It's not a question.

"I want this."

"Lie back."

I lie back on the dark sheets, and the lace bra pushes against my chest, and the panties are stretched tight over my erection. Matissa produces a bottle of lube from the nightstand — because of course Tyson stocked the nightstand — and the petite one helps slide my panties down my legs.

"Leave the bra on," you say, and your voice is rough.

Matissa pushes my legs apart and kneels between them. Her cock is slick with lube, and she presses a wet finger against my asshole, and I tense.

"Relax," she says. "Breathe."

I breathe. You're lying beside me now, your hand on my chest, your fingers tracing the lace. You lean down and kiss me, and your tongue is in my mouth, and I feel Matissa's finger slide inside me.

It's uncomfortable. It's strange. It's also electric — a sensation that radiates outward and meets the pleasure from your kiss and creates something entirely new. She adds a second finger, and I groan into your mouth.

"Ready?" Matissa asks.

"Ready," I say, and I'm not sure if I am, but I don't care.

She replaces her fingers with the head of her cock, and she pushes in slowly, so slowly, and the stretch is intense and foreign and I'm gripping the sheets with both hands. You're whispering in my ear — dirty things, sweet things, things like "you look so fucking good" and "take it, take all of it" — and then she's inside me fully, and I feel full in a way I've never felt before.

She starts to move. Slow at first, long deliberate strokes that make me gasp each time she pulls back and pushes forward. Then faster, finding a rhythm, and I hear myself making sounds I've never made — guttural, animal sounds that echo off the walls.

Meanwhile, the other three have gathered close. The slim one is standing at the edge of the bed near my head, stroking his cock with long, deliberate pulls. The broad one is on the other side, his thick dick in his fist. The petite one is at the foot of the bed, watching Matissa fuck me while jerking off.

"Open your mouth," you say, and I do.

The slim one steps closer, and the head of his cock brushes my lips. I take him in while Matissa fucks me, and now I'm being filled from both ends, and the sensation is so intense that I think I might come just from this — from the friction of the lace bra on my nipples and the cock in my ass and the cock in my mouth and your hands on my chest and your voice in my ear.

Matissa is fucking me harder now, her thighs slapping against mine, her breathing ragged. "I'm close," she says.

"Come inside him," you say, and I feel your hand wrap around my cock, and you start stroking me in time with Matissa's thrusts.

I come first. The orgasm hits me like a wave — no, like a wall, like a fucking building collapse — and I shoot across my stomach and your hand and the black lace bra, and my ass clenches around Matissa's cock, and she groans and pushes deep and comes inside me.

I feel it. The hot pulse of it, filling me up, and it's the filthiest and most incredible thing I've ever experienced.

She pulls out slowly, and I feel the wet trickle down my thigh. The slim one pulls out of my mouth, and I'm gasping, lying there wrecked and satisfied and still wearing your bra.

But the night isn't over.

You sit up and look at the three cross-dressers standing around the bed. "Finish on his face," you say, and your tone leaves no room for negotiation.

Matissa, recovered, joins them. She's stroking herself again, her cock still slick with lube and my ass, and the four of them stand over me while you settle back in the chair, your hand between your legs again.

I lie still, looking up at them — four hard cocks above me, four sets of hands working, four cross-dressers in various states of lingerie and undress. The petite one comes first, with a sharp cry, and his cum lands on my cheek and my lips. I lick it off, tasting salt and bitterness, and someone groans.

The broad one is next, his thick cock erupting across my forehead and the bridge of my nose. It's warm and viscous, and I feel it slide down toward my eye, and I close my eyes and open my mouth.

The slim one comes with a grunt, his load landing on my tongue and chin, thick and copious. I swallow what lands in my mouth and feel the rest drip down my neck.

Matissa is last. She strokes herself with purpose, her eyes locked on my cum-covered face, and when she comes, it's across my lips and chin, mixing with the others.

I lie there, breathless, face covered in cum, ass full of cum, wearing a bra and the afterglow of the most intense orgasm of my fifty years.

"Clean up," you say, and you're standing over me now, and you're smiling. "Eat it."

I use my fingers to scoop the cum from my face, and I bring each load to my mouth and swallow. It's bitter and salty and strange and I love it — every drop, every smear, every trace. I clean my face methodically, licking my fingers, and you watch the whole time, your eyes dark with satisfaction.

When I'm done, you lie down beside me on the dark sheets and press your lips to mine. You don't care about the residue. You kiss me deep, and I taste your tongue and the faint remnant of four cross-dressers, and it's perfect.

"Happy birthday, Mark," you say.

"Best fucking birthday I've ever had."

Downstairs, the music is still playing. Someone is laughing. Tyson is probably telling everyone about the old guy in the black bra who finally let go. I don't care. I'm lying in a king-sized bed in a stranger's mansion, wearing lingerie you gave me, with your lips on my neck and the memory of cock in my mouth and ass, and I'm fifty years old and I've never felt more alive.

"You know," I say, "I think I need a bigger bra size."

You laugh so hard you snort, and Matissa, pulling her babydoll back on in the corner, laughs too.

"I'll take you to Kayla's shop tomorrow," you say. "She'll measure you properly."

I close my eyes. Your hand is on my chest, resting on the lace, and I feel the steady thump of my heart against your palm.

Fifty, I think. Not a bad start to the next fifty.